• Bulletin of the Korean Chemical Society
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• v.35 no.6
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• pp.1809-1816
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• 2014

This study demonstrates gel-to-fluid transition temperatures of polydiacetylene bilayer vesicles could play important roles in their colorimetric transition temperatures. We prepared five types of polydiaceylene vesicles with 10,12-pentacosadiynoic acid (PCDA) and cholesterol (0-40 mol % of total content). From temperature-dependent observations of the optical signals (colors and UV-vis spectra), the blue-to-red colorimetric transition temperatures of polydiacetylene vesicles were decreased with the cholesterol contents. A further study with microcalorimetry and dynamic light scattering revealed that the polydiacetylene vesicles first underwent gel-to-fluid transitions, which were followed by event(s) responsible for the colorimetric transitions. Energies required for each event were quantified from analysis of the peaks in the microcalorimetry thermograms. The inclusion of cholesterol in the vesicles decreased both the gel-to-fluid and the colorimetric transition temperatures, suggesting that the colorimetric transition of the polydiacetylene vesicles was mediated by the former event although the event was not the direct reason for the color change.

• Bulletin of the Korean Chemical Society
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• v.34 no.10
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• pp.3083-3087
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• 2013

Diacetylene lipid monomers possess the capability to self-assemble into vesicles via polymerization under ultraviolet irradiation, resulting in the formation of polydiacetylene (PDA) liposomes. Exposure of the polymerized vesicles to external stimuli is known to induce a unique blue-to-red color transition. The cyclic oligosaccharide ${\alpha}$-cyclodextrin known for its use in many applications, such as drug delivery, purification, and stimulus sensing, is able to form an inclusion complex with poly(ethylene glycol) (PEG) in aqueous solution. In this study, we prepared polymeric liposomes with PEG (PEG-PDA) with the aim of improving the stability of the vesicles and colorimetric response toward ${\alpha}$-cyclodextrin. We demonstrated that PEG-PDA liposome displays unique characteristics compared with native PDA liposome and it also shows apparent chromic properties of the inclusion complex formation with ${\alpha}$-cyclodextrin.

• Applied Chemistry for Engineering
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• v.34 no.6
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• pp.660-664
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• 2023

In this study, a new system to determine the concentration of cholesterol using a color change was developed. The system comprised diacetylene vesicles and cholesterol oxidase (ChOx). 10,12-Pentacosadiynoic acid (PCDA) was used as the diacetylene compound, and PCDA vesicles were formed using sonication. The H₂O₂ produced during the reaction between cholesterol and ChOx was used to initiate the polymerization of the PCDA in the vesicles. During polymerization, the vesicles changed from colorless to blue. Therefore, the cholesterol concentration was proportional to the intensity of the blue color. The absorption at 665 nm indicated that the blue color was directly proportional to the cholesterol concentration. This indicates that the system can be used for cholesterol detection. The minimum cholesterol concentration detected using this system was 1.0 mM.

• Korean Chemical Engineering Research
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• v.49 no.4
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• pp.400-404
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• 2011

Many studies on polydiacetylene(PDA) have been investigated to apply to chemical and biological sensors due to their unique optical properties of color change from blue to red and fluorescence change from non-fluorescence to red fluorescence. Especially, high sensitivity against specific molecules is very important to apply polydiacetylenes to various sensors. In this study, we examined the effect of sensitivity enhancement of 10,12-pentacosadynoic acid(PCDA) vesicles in detection ${\alpha}$-cyclodextrin(CD) according to control of vesicle size by filters with different pore sizes and polymerization temperature. Colorimetric response(CR) was calculated using visible spectrometer. In order to investigate the effect of vesicle size on sensitivity of PDA vesicles, two PCDA vesicles were filtered without filtration and with 0.22 ${\mu}m$ filter. The two PCDA vesicles were polymerized at $25^{\circ}C$ and were incubated with ${\alpha}$-CD(5 mM) for 30 min. The CRs of the former and latter vesicles were 31.4% and 74.0%, respectively. Then, two PCDA vesicles filtered with 0.22 ${\mu}m$ filter were polymerized at $25^{\circ}C$ and $5^{\circ}C$ and were reacted with ${\alpha}$-CD(5 mM) for 30 min to examine the effect of polymerization temperature. The CRs of the former and latter vesicles were 74.0 and 99.2%, respectively. This suggests that vesicle sizes and polymerization temperature are key factors in enhancing the sensitivity of PDA vesicles. In addition, these results are expected to be useful to apply the PDA vesicles as biosensors to detect DNA, protein, and cells.

• Macromolecular Research
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• v.14 no.4
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• pp.478-482
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• 2006

• Korean Chemical Engineering Research
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• v.49 no.3
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• pp.348-351
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• 2011

In this research, we developed a sensor system which can easily detect several chelating agents using polydiacetylene(PDA) vesicles. In comparison to other sensors, PDA based sensor has several advantages. First, detection method is much simpler and faster because it does not require any labeling step in the experiment procedure. Second, significant color-transition from blue to red based upon external stimulus allows us the detection by naked eyes. Finally, it is also possible to perform quantitative analysis of the concentration of the chelating agent by measuring the colorimetric response. In this paper, five types of chelating agents were used, including EDTA, EGTA, NTA, DCTA and DTPA. Among them, EDTA and DCTA triggered especially strong color-transition. In conclusion, this study has led to a successful development of a color transition-based PDA sensor system for easy and rapid detection of chelating agents.

• 한국생물공학회:학술대회논문집
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• 2005.04a
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• pp.494-494
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• 2005

• Proceedings of the Polymer Society of Korea Conference
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• 2006.10a
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• pp.306-306
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• 2006

We immobilized and patterned PDA vesicles on solid substrate using micro arrayer, which have moieties to react with chemical and biological materials. Immobilized vesicle system was developed since it possesses many advantages in multiple screening, durable stability, and higher sensitivity. We applied polydiacetylene supramolecules to chemical and biological sensors for detection of ${\alpha}-cyclodextrin$ and E.coli cell selectively. This detection method could be applied as DNA chip, protein chip, and cell chip for multiple screening as well as chemical sensor by modifying the functional groups of diacetylene monomer.

• Macromolecular Research
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• v.13 no.3
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• pp.253-256
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• 2005

We prepared amino acid-derived diacetylene monomers using solid-phase organic synthesis. The solid-phase synthetic method allowed for the rapid and efficient preparation of functional diacetylenes. Amino acids having hydrophobic sidechains such as alanine, leucine, and phenylalanine, as well as hydrophilic sidechains such as aspartic acid and lysine, were successfully coupled to the diacetylene lipid. The diacetylene monomers prepared in this way were subjected to routine procedures for the generation of polydiacetylene vesicles. Depending on the nature of the side-chains, pink to blue colored polydiacetylenes were generated.